From an online discussion:
Speak up about sharing dating expenses
Q: How does one person who is extremely frugal begin to date someone who has a lot of money and enjoys doing expensive things? This seems like such a ridiculous reason for not being able to date someone. I am just out of school, in my first job — not a huge budget but good enough. Also, I should mention that while I am female and am speaking of dating a man, I feel very uncomfortable expecting that a man you are dating would pay for things. It is nice when someone makes that offer, but I do not like to go to something if I do not have the money to pay for it.
Also, this is very, very new, and to bring up a discussion of money feels out of context at this point.
A: I trust you that the context hasn't allowed this yet, but I do think the situations you describe will present some openings. Such as, "I'd love to go to X, but there's no way I can afford it. Can we try Y instead?" Then, if he says it's on him, do thank him — and even accept, if that's what you want to do, since there is no quid pro quo in dating. However, please also realize this is your opportunity to say that it's important to you to . . . whatever. Pay your own way occasionally/half the time/every time? Alternate with plans you can afford?
It may feel premature to state your philosophy, but since you also feel weird not saying anything, it might be better just to speak up — and even admit "it feels premature to say this, but please humor me."
Taking turns paying comes later
Q: I feel like my last three dates were totally turned off by the fact that I wanted to pay my way on pretty much everything. Once I'm in a relationship, I feel comfortable taking turns but when things are new I really don't like the feeling of "owing" a person for anything.
A: An argument for speaking up early, if I've ever seen one. For what it's worth, one way to know you're in a healthy relationship, however new, is when "the feeling of 'owing' " isn't there.
Invitations are not top priority
Q: The wedding invitation is so important. I would encourage brides to get it right. Wrong is tacky, ordinary stamps, misspelled guest names, and bows that are dirty and poorly tied. My cousins have sent some especially low-rent invites so I feel like I have seen it all. Show some pride. My parents spent a tremendous amount on mine and they were gorgeous.
A: Well then, count yourself lucky you had parents with sufficient time and means (so often intertwined) to make a big deal of your invitations. Other couples have to pick their priorities, and surely you agree that the top priority is the quality of the relationship between bride and groom. I'm more than happy to celebrate that kind of union, even if I'm invited by e-mail.